Constituents of Cupuliferae,XVII: Triterpene Saponins and Falvonoids from Quercus laurifolia Michx.

In addition to fourteen known glycosides from leaves of Quercus laurifolia Michx., a new acylated triterpene soponin has been isolated and identified as 3-O-galloyl-28-β-D -glucopyranosyl diester of the 2α,3β,19α,23-tetrahydroxyurs-12-ene-28-oic acid ( 1 ). The structure of the previously described α-D -glucopyranosyl ester of the 2α,3β,19α,23-tetrahydroxyurs-12-ene-28-oic acid was revised to β-D -glucopyranosyl ester of the 2α,3β,19α,23-tetrahydroxyurs-12-ene-28-oic acid ( 2 ).     

Unusual microbial lactonization and hydroxylation of asiatic acid by Umbelopsis isabellina

Asiatic acid (1) is a natural triterpenoid isolated from Centella asiatica. This paper reports the microbial transformation of asiatic acid by an endophytic fungus Umbelopsis isabellina to obtain derivatives potentially useful for further studies. Incubation of asiatic acid with U. isabellina afforded two derivatives 2α,3β,7β, 23-tetrahydroxyurs-12-ene-28-oic acid (2) and 2α,3β,7β,23-tetrahydroxyurs-11-ene-28,13-lactone (3). The structures of these compounds were elucidated by spectral data. Compound 3 has formed an unusual lactone. These two products are new compounds. The possible transformation passway was also discussed.     

Microbial transformation of the anti-diabetic agent corosolic acid by Cunninghamella echinulata

The pentacyclic triterpenoid corosolic acid was metabolized by Cunninghamella echinulata CGMCC 3.2000 to its C-24 aldehyde group metabolite and five other hydroxylated metabolites: madasiatic acid (2), 2α, 3β, 7β-trihydroxyurs-12-en-28-oic acid (3), 2α, 3β, 15α-trihydroxyurs-12-en-28-oic acid (4), 2α, 3β, 6β, 7β-tetrahydroxyurs-12-en-28-oic acid (5), 2α, 3β, 7β, 15α-tetrahydroxyurs-12-en-28-oic acid (6), and 2α, 3β,7β-trihydroxy-24-al-urs-12-en-28-oic acid (7); compounds 3, 5, and 7 were new compounds. The α-glucosidase inhibitory effects of the metabolites were also evaluated.     

New ursane-type triterpene with NO production suppressing activity from Nauclea officinalis

Two new ursane-type triterpenes, named as 3β,?19α,?23,?24-tetrahydroxyurs-12-en-28-oic acid (1) and 2β,?3β,?19α,?24-tetrahydroxyurs-12-en-28-oic acid (2), together with two known triterpenoids, 3-oxo-urs-12-ene-27, 28-dioic acid (3) and quinovic acid-3-β-rhamnopyranoside (4), were isolated from the stems (with barks) of Nauclea officinalis. The structures of 1 and 2 were determined by the combined use of single-crystal X-ray diffraction and spectroscopic data analysis. The inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells were examined, and compound 1 was found to inhibit NO production, with the IC(50) value of 4.8?μM.     

Two new triterpenoids from Callicarpa kwangtungensis

Two new triterpenoids, 2α,3β,16α,19α,23-pentahydroxyolean-12-en-28-oic acid (1) and 2α,3α,11α,21α,23-pentahydroxyurs-12-en-28-oic acid (2), were isolated from the aerial parts of Callicarpa kwangtungensis. Their structures were elucidated by 1D and 2D analyses, as well as MS and IR spectra.     

藤山柳根茎中的三萜成分

目的　研究我国特有的单种属药用植物藤山柳[Clematoclethrascandens (Franch .)Maxim .]根茎的甲醇提取物正丁醇萃取部分的化学成分。方法　将甲醇提取物分散于水中,经石油醚和乙酸乙酯萃取后,再用正丁醇进行萃取,对正丁醇萃取物进行柱色谱分离纯化,用波谱方法鉴定化合物结构。结果　分离鉴定了5个三萜化合物:2α,3β,24-三羟基乌苏-12 ,18-二烯-28-酸-28-O-β-D-吡喃葡糖酯(I) ,niga-ichigoside F₁ (II) ,asiaticacid (III) ,2α,3α,24-三羟基乌苏-12-烯-28-酸(IV) ,2α,3α,19α,24-四羟基乌苏-12-烯-28-酸(V)。结论　以上三萜化合物均为首次从该属植物中获得,其中I是一个新三萜皂苷     

旱莲草化学成分旱莲甙A和旱莲甙B的分离和鉴定

自旱莲草(Eclipta alba(L.)Hassk)全草中分得4个三萜化合物,经理化常数测定和光谱(IR,MS,UV,¹HNMR,¹³CNMR和¹³C-¹HCOSY)解析,2个已知的三萜类化合物分别为刺囊酸(echinocysticacid,I)和齐墩果酸(oleanlicacid,II),另2个为新化合物,分别命名为旱莲甙A(eclip-tasaponinA,II)和旱莲甙B(ecliptasaponinB,IV)。I和II为首次从鳢肠属植物中获得。     

Microbial transformation of oleanolic acid by Trichothecium roseum

Microbial transformation of the oleanolic acid (1) using Trichothecium roseum (pers.) Link (M 95.56) has resulted in the isolation of two new hydroxylated type metabolites, characterized as 15α-hydroxy-3-oxo-olean-12-en-28-oic acid (2) and 7β,15α-dihydroxy-3-oxo-olean-12-en-28-oic acid (3). The structure elucidation of these metabolites was based primarily on HR-EIMS, 1D NMR, and 2D NMR analyses.     

Puberosides C–E,triterpenoid saponins from Glochidion puberum

Three new triterpenoid glycosides, named puberosides C–E (1–3), were isolated from the water-soluble fraction of Glochidion puberum (Linn.) Hutch. Their structures were determined as 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-trans-cinnamoyl-olean-12-ene-16α,28-diol, 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-cis-cinnamoyl-olean-12-ene-16α,28-diol, and 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-β-d-glucopyranosyl)oxy]-22α-benzoyloxy-olean-12-ene-16α,28-diol by the combination of 1D, 2D NMR, and MS spectral analyses.     

Four new taraxastane-type triterpenoic acids from Cirsium setosum

Four new taraxastane-type triterpenoids acids 3β,22α-dihydroxy-20-taraxasten-30-oic acid (1), 3β-hydroxy-22-oxo-20-taraxasten-30-oic acid (2), 3-oxo-22α-hydroxy-20- taraxasten-30-oic acid (3), and 3β,19β-dihydroxy-20-taraxasten-30-oic acid (4) were isolated and characterized from Cirsium setosum (Willd.) MB. Their structures were determined by the combination of 1D and 2D NMR experiments (¹H-¹HCOSY, HSQC, HMBC and ROESY) and mass spectrometry. Compound 2 exhibited potent selective cytotoxicity against human ovarian cancer cell line A2780 with an IC₅₀ value of 3.9 μM.     

Four new triterpenoid glycosides from the seed residue of Hippophae rhamnoides subsp. sinensis

Four new triterpenoid saponins (1–4) were isolated from the seed residue of Hippophae rhamnoides subsp. sinensis, named 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-13-ene-19-one-28-oic acid 28-O-β-d-glucopyranosyl ester (1), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-β-d-glucopyranosyl ester (2), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl-13-ene-19-one-28-oic acid 28-O-β-d-glucopyranosyl ester (3), and 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-β-d-glucopyranosyl ester (4), and their structures were elucidated on the basis of spectroscopic and chemical methods.     

Chemical constituents of the twigs and leaves of Erythrina strica

A total of 15 compounds were extracted from the ethyl acetate extraction of the twigs and leaves of Erythrina strica. Based on NMR spectral data, their structures were identified as loliolide (1), phaseic acid (2), pinnatififidanoid A (3), soyasapogenol E (4), soyasapogenol B (5), 2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid (6), 3β,22β,24-trihydroxyolean-12-en-29-oic acid (oxytrogenin) (7), (23Z)-9,19-cycloart-23-ene-3β,25-diol (8), 3,4-dihydroxybenzoic acid (9), syringaresinol (10), (E)-4-hydroxy-dodec-2-enedioic acid (11), lutein (12), ergosterol-5,8-peroxide (13), β-sitosterol (14), and daucosterol (15). Except for compounds 13–15, all the compounds were isolated from this plant for the first time. Moreover, sesquiterpenoids were isolated from Erythrina genus for the first time.     

Microbial transformation of hederagenin by Cunninghamella echinulate,Mucor subtilissimus,and Pseudomonas oleovorans

The pentacyclic triterpenoid hederagenin (1) was subjected to biotransformation by Cunninghamella echinulate CGMCC 3.2000, Mucor subtilissimus CGMCC 3.2454 and Pseudomonas oleovorans CGMCC 1.1641. Three metabolites were obtained. On the basis of nuclear magnetic resonance and high-resolution mass spectral analyses, their structures were characterized as 3β, 23-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3β, 15α, 23-trihydroxyolean-12-en-28-oic acid (3), 1β, 3β, 23-trihydroxyolean-12-en-28-oic acid (4), and metabolite (3) was a new compound. This was the first report on the biotransformation of hederagenin.     

Triterpenes from Astilbe chinensis

Six new triterpenes, 3β,6β-dihydroxyurs-12-en-27-oic acid (1), 3β,6β,24-trihydroxyurs-12-en-27-oic acid (2), 3β,6β,7α-trihydroxyurs-12-en-27-oic acid (3), 3β-acetoxy-6β-hydroxyurs-12-en-27-oic acid (4), 3β,6β,24-trihydroxyolean-12-en-27-oic acid (5), and 3β,6β,7α-trihydroxyolean-12-en-27-oic acid (6), were isolated from the rhizomes of Astilbe chinensis. Their structures were elucidated on the basis of 1D- and 2D-NMR analyses and HR-MS experiments. The isolated compounds exhibited significant cytotoxic activities against the SK-N-SH and HL-60 cell lines.     

A new ursane-type triterpene,cymosic acid from Rosa cymosa

A new ursane-type triterpene, cymosic acid (1) together with two known compounds, 3β,19α-dihydroxy-2-oxo-12-ursen-28-oic acid (2) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (3), were isolated from Rosa cymosa Tratt. The structure of compound 1 was elucidated by analyzing its ¹H and ¹³C NMR, ¹H–¹H COSY, HSQC, HMBC, NOESY, and HR-ESI-MS values. The three compounds were found to display moderate inhibitory activities against nitric oxide production in lipopolysaccharide-activated macrophage cell lines, RAW 264.7 cells.     

New compounds with antimicrobial activities from Elaeodendron buchananii stem bark

The plant species Elaeodendron buchananii Loes is widely used in folklore medicine to manage microbial infections in Kenya. Previous studies on the plant fruits and root bark revealed the presence of steroids and terpenoids. The present phytochemical analysis of the plant stem bark has led to the isolation of four new triterpenes characterized as methyl 3β-acetoxy-11α, 19α, 28-trihydroxyurs-12-en-23-oic acid (1), 3β, 11α, 19α-trihydroxyurs-12-en-23, 28-dioic acid (2), 3β-acetoxy-19α, 23, 28-trihydroxyurs-12-ene (3) and 3-oxo-19α, 28-dihydroxyurs-12-en-24-oic acid (4), together with ten known ones (5–14), whose structures were elucidated using spectroscopic techniques. The isolate canophyllol (8) showed promising antibacterial activity against N. meningitides with MIC value of 31.25 μg/ml.     

刺梨酸的分离与结构研究

从刺梨中分离出一种新的五环三萜酸,命名为刺梨酸。通过光谱分析和衍生物的制备,确定其化学结构为2β,3α,7β,19α-四羟基乌苏-12-烯-28-羧酸。     

Two new triterpenoid glycosides from the leaves of Anthocephalus chinensis

Nine compounds were isolated from the leaves of Anthocephalus chinensis by column chromatography on silica gel and Sephadex LH-20, and their structures were elucidated by spectroscopic techniques as clethric acid-28-O-β-d-glucopyranosyl ester (1), mussaendoside T (2), β-stigmasterol (3), hederagenin (4), ursolic acid (5), clethric acid (6), 3β,6β,19α,24-tetrahydroxyurs-12-en-28-oic acid (7), mussaendoside I (8), and cadambine (9). Compounds 1 and 2, and 7 and 8 were isolated from the plants of this genus for the first time, and compounds 1 and 2 were new triterpenoid glycosides.     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

Two new triterpenoid saponins from Symplocos Chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21β-O- cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (1) and 21β-O-cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-(3-O-acetyl)-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.